In 1861, a charter was given to the Chicago and Evanston Railroad; however, the line began operation on May 1, 1885, after many years of funding and land acquisition problems.

[3][4] Initially, the line ran from the intersection of Chicago Avenue and Larrabee Street to a station at the Calvary Cemetery.

Earlier in 1907, the Northwestern Elevated Railroad Company made an agreement with Milwaukee Road to operate "L" service to Evanston, which opened in 1908.

[11] Gauntlet tracks were added to avoid crashing into freight trains, station platforms, and third rails.

[11] In many years since, more sections of the C&E were removed, including a river crossing to/from Chicago Union Station (demolished in 1973) and much of the street-running track.

[12][4] In 1985, the Soo Line Railroad (now a subsidiary of the CPKC Railway) acquired the bankrupt Milwaukee Road, including its Evanston Division (C&E).

[13] In 2007, the Chicago Terminal Railroad (CTM) acquired the remaining segment of the C&E between Division Street and Diversey Parkway.

[16] The track south of North Avenue was removed in 2012 as part of a beautification project at Kingsbury Street.

[12] The City of Chicago eventually acquired the C&E tracks from CTM in 2019 after the latter ceased operation a year earlier.